US8383824B2 - Heterocyclic antiviral compounds - Google Patents
Heterocyclic antiviral compounds Download PDFInfo
- Publication number
- US8383824B2 US8383824B2 US12/950,127 US95012710A US8383824B2 US 8383824 B2 US8383824 B2 US 8383824B2 US 95012710 A US95012710 A US 95012710A US 8383824 B2 US8383824 B2 US 8383824B2
- Authority
- US
- United States
- Prior art keywords
- alkyl
- phenyl
- hydrogen
- hcv
- pyridin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related, expires
Links
- 0 [1*]C1=CC([3*])=CC(C(C([2H])([2H])[2H])(C([2H])([2H])[2H])C([2H])([2H])[2H])=C1[2*] Chemical compound [1*]C1=CC([3*])=CC(C(C([2H])([2H])[2H])(C([2H])([2H])[2H])C([2H])([2H])[2H])=C1[2*] 0.000 description 13
- BQSUJCRHKVTWSU-ZHACJKMWSA-N COC1=C(C(C)(C)C)C=C(C2=CC=CCC2=O)C=C1/C=C/C1=C(CO)C=C(NS(C)(=O)=O)C=C1 Chemical compound COC1=C(C(C)(C)C)C=C(C2=CC=CCC2=O)C=C1/C=C/C1=C(CO)C=C(NS(C)(=O)=O)C=C1 BQSUJCRHKVTWSU-ZHACJKMWSA-N 0.000 description 1
- TXTPQCQRLUYZRU-DHVPFICPSA-N O=C=O.[2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=C(C)C=C(NS(C)(=O)=O)C=C2)=CC(C2=CC=CCC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H] Chemical compound O=C=O.[2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=C(C)C=C(NS(C)(=O)=O)C=C2)=CC(C2=CC=CCC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H] TXTPQCQRLUYZRU-DHVPFICPSA-N 0.000 description 1
- KKKIOEHMQWIJMO-XTFMRPKQSA-N O=C=O.[H]C1=C(/C=C/C2=CC(C3=CC=CCC3=O)=CC(C(C([2H])([2H])[2H])(C([2H])([2H])[2H])C([2H])([2H])[2H])=C2OC)C=CC(NS(C)(=O)=O)=C1 Chemical compound O=C=O.[H]C1=C(/C=C/C2=CC(C3=CC=CCC3=O)=CC(C(C([2H])([2H])[2H])(C([2H])([2H])[2H])C([2H])([2H])[2H])=C2OC)C=CC(NS(C)(=O)=O)=C1 KKKIOEHMQWIJMO-XTFMRPKQSA-N 0.000 description 1
- CDULKKYQVFREKE-QFQSILKMSA-N [2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=CC=C(NS(C)(=O)=O)C=C2)=CC(C2=CC(Cl)=CCC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H] Chemical compound [2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=CC=C(NS(C)(=O)=O)C=C2)=CC(C2=CC(Cl)=CCC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H] CDULKKYQVFREKE-QFQSILKMSA-N 0.000 description 1
- VONJRPKXIZJNAD-FKGBSCMGSA-N [2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=CC=C(NS(C)(=O)=O)C=C2)=CC(C2=CC=C(C)CC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H] Chemical compound [2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=CC=C(NS(C)(=O)=O)C=C2)=CC(C2=CC=C(C)CC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H] VONJRPKXIZJNAD-FKGBSCMGSA-N 0.000 description 1
- QBRSQOAXFDWRCV-XTFMRPKQSA-N [2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=CC=C(NS(C)(=O)=O)C=C2)=CC(C2=CC=CCC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H].[HH] Chemical compound [2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=CC=C(NS(C)(=O)=O)C=C2)=CC(C2=CC=CCC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H].[HH] QBRSQOAXFDWRCV-XTFMRPKQSA-N 0.000 description 1
- AWZHPPFIRPKTIE-QFQSILKMSA-N [2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=CC=C(NS(C)(=O)=O)C=C2)=CC(C2=CNC(=O)CC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H] Chemical compound [2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=CC=C(NS(C)(=O)=O)C=C2)=CC(C2=CNC(=O)CC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H] AWZHPPFIRPKTIE-QFQSILKMSA-N 0.000 description 1
- VJMFCDMMFJSQAQ-QFQSILKMSA-N [2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=CC=C(NS(C)(=O)=O)C=C2)=CC(C2=NC=NCC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H] Chemical compound [2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=CC=C(NS(C)(=O)=O)C=C2)=CC(C2=NC=NCC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H] VJMFCDMMFJSQAQ-QFQSILKMSA-N 0.000 description 1
- PWIPBAYVQPQHTB-VSCFNVETSA-N [2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=CC=C(NS(C)(=O)=O)C=C2COC)=CC(C2=CC=CCC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H] Chemical compound [2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=CC=C(NS(C)(=O)=O)C=C2COC)=CC(C2=CC=CCC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H] PWIPBAYVQPQHTB-VSCFNVETSA-N 0.000 description 1
- VGQWPDZZRYMRFS-CLQNVJIPSA-N [2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=CC=C(NS(C)(=O)=O)C=C2F)=CC(C2=CC(F)=CCC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H] Chemical compound [2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=CC=C(NS(C)(=O)=O)C=C2F)=CC(C2=CC(F)=CCC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H] VGQWPDZZRYMRFS-CLQNVJIPSA-N 0.000 description 1
- OSZRYRYFLBPJNB-JMJWVMKQSA-N [2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=CC=C(NS(C)(=O)=O)C=N2)=CC(C2=CC(Cl)=CCC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H] Chemical compound [2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=CC=C(NS(C)(=O)=O)C=N2)=CC(C2=CC(Cl)=CCC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H] OSZRYRYFLBPJNB-JMJWVMKQSA-N 0.000 description 1
- YHLSTHRHXDZNMX-UUWRFDLFSA-N [2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=CC=C(NS(C)(=O)=O)N=C2)=CC(C2=CC=CCC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H] Chemical compound [2H]C([2H])([2H])C(C1=C(OC)C(/C=C/C2=CC=C(NS(C)(=O)=O)N=C2)=CC(C2=CC=CCC2=O)=C1)(C([2H])([2H])[2H])C([2H])([2H])[2H] YHLSTHRHXDZNMX-UUWRFDLFSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4412—Non condensed pyridines; Hydrogenated derivatives thereof having oxo groups directly attached to the heterocyclic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Virology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Gastroenterology & Hepatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/950,127 US8383824B2 (en) | 2009-11-21 | 2010-11-19 | Heterocyclic antiviral compounds |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US26335009P | 2009-11-21 | 2009-11-21 | |
US12/950,127 US8383824B2 (en) | 2009-11-21 | 2010-11-19 | Heterocyclic antiviral compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
US20110123489A1 US20110123489A1 (en) | 2011-05-26 |
US8383824B2 true US8383824B2 (en) | 2013-02-26 |
Family
ID=43446565
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12/950,127 Expired - Fee Related US8383824B2 (en) | 2009-11-21 | 2010-11-19 | Heterocyclic antiviral compounds |
Country Status (11)
Country | Link |
---|---|
US (1) | US8383824B2 (pt) |
EP (1) | EP2501679A1 (pt) |
JP (1) | JP2013511489A (pt) |
KR (1) | KR20120085918A (pt) |
CN (1) | CN102639504A (pt) |
AR (1) | AR079076A1 (pt) |
BR (1) | BR112012012085A2 (pt) |
CA (1) | CA2778206A1 (pt) |
MX (1) | MX2012005706A (pt) |
TW (1) | TW201129362A (pt) |
WO (1) | WO2011061243A1 (pt) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102014217907B4 (de) | 2014-09-08 | 2018-12-20 | Carl Zeiss Smt Gmbh | Verfahren zum Herstellen einer Maske für den extrem ultra-violetten Wellenlängenbereich und Maske |
US9765050B2 (en) | 2014-12-30 | 2017-09-19 | Novira Therapeutics, Inc. | Pyridyl reverse sulfonamides for HBV treatment |
Citations (10)
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US7517990B2 (en) * | 2002-11-15 | 2009-04-14 | Wako Pure Chemical Industries, Ltd. | Method for deuteration of a heterocyclic ring |
US20100021423A1 (en) * | 2008-07-23 | 2010-01-28 | Roche Palo Alto Llc | Heterocyclic antiviral compounds |
WO2010072598A1 (en) | 2008-12-22 | 2010-07-01 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
WO2010111436A2 (en) | 2009-03-25 | 2010-09-30 | Abbott Laboratories | Antiviral compounds and uses thereof |
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JP3373502B2 (ja) | 1999-12-24 | 2003-02-04 | 旭硝子株式会社 | 窒化ケイ素フィルタおよびその製造法 |
EP1292310A1 (en) | 2000-05-10 | 2003-03-19 | SmithKline Beecham Corporation | Novel anti-infectives |
US6448281B1 (en) | 2000-07-06 | 2002-09-10 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
AR036081A1 (es) | 2001-06-07 | 2004-08-11 | Smithkline Beecham Corp | Compuesto de 1,2-dihidroquinolina, su uso para preparar una composicion farmaceutica, metodos para prepararlo y compuestos del acido 2-aminobenzoico n-alquilado de utilidad como intermediarios en dichos metodos |
AR035543A1 (es) | 2001-06-26 | 2004-06-16 | Japan Tobacco Inc | Agente terapeutico para la hepatitis c que comprende un compuesto de anillo condensado, compuesto de anillo condensado, composicion farmaceutica que lo comprende, compuestos de benzimidazol, tiazol y bifenilo utiles como intermediarios para producir dichos compuestos, uso del compuesto de anillo con |
EP1411928A1 (en) | 2001-07-20 | 2004-04-28 | Boehringer Ingelheim (Canada) Ltd. | Viral polymerase inhibitors |
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WO2003099801A1 (en) | 2002-05-24 | 2003-12-04 | Smithkline Beecham Corporation | Novel anti-infectives |
JP5008258B2 (ja) * | 2002-06-20 | 2012-08-22 | アイシー・ベック・リミテッド | 含硫黄ホスホリピド誘導体 |
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2010
- 2010-11-18 EP EP10777032A patent/EP2501679A1/en not_active Withdrawn
- 2010-11-18 KR KR1020127015923A patent/KR20120085918A/ko not_active Application Discontinuation
- 2010-11-18 WO PCT/EP2010/067718 patent/WO2011061243A1/en active Application Filing
- 2010-11-18 CA CA2778206A patent/CA2778206A1/en not_active Abandoned
- 2010-11-18 CN CN2010800526144A patent/CN102639504A/zh active Pending
- 2010-11-18 BR BR112012012085A patent/BR112012012085A2/pt not_active Application Discontinuation
- 2010-11-18 JP JP2012539323A patent/JP2013511489A/ja active Pending
- 2010-11-18 MX MX2012005706A patent/MX2012005706A/es not_active Application Discontinuation
- 2010-11-18 TW TW099139810A patent/TW201129362A/zh unknown
- 2010-11-19 US US12/950,127 patent/US8383824B2/en not_active Expired - Fee Related
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Also Published As
Publication number | Publication date |
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JP2013511489A (ja) | 2013-04-04 |
KR20120085918A (ko) | 2012-08-01 |
AR079076A1 (es) | 2011-12-21 |
WO2011061243A1 (en) | 2011-05-26 |
US20110123489A1 (en) | 2011-05-26 |
BR112012012085A2 (pt) | 2016-05-17 |
MX2012005706A (es) | 2012-06-12 |
CN102639504A (zh) | 2012-08-15 |
TW201129362A (en) | 2011-09-01 |
CA2778206A1 (en) | 2011-05-26 |
EP2501679A1 (en) | 2012-09-26 |
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